Ammonia → Bis(2-pyridyl)methylamine

To pyridyl ketone oxim (3 g, 15.1 mmol) was added ethanol (15 ml), concentrated ammonia solution (15 mL) and NH4OAc (1.21 g, 15.8 mmol). The solution was warmed until reflux. To this solution was added 4.64 g Zn in small portions. After the addition of all Zn, the mixture was refluxed for 1 hour and allowed to cool to ambient temperature. The solution was filtered and water (15 ml) was added. Solid NaOH was added until pH>>10 and the solution was extracted with CH2Cl2 (3×20 ml). The organic layers were dried over Na2SO4 and evaporated until dryness. Bis(pyridin-2-yl)methylamine (2.39 g, 12.9 mmol) was obtained as a colourless oil in 86% yield, showing the following analytical characteristics:

1. temperatureThe solution was warmed
2. temperatureuntil reflux
3. temperaturethe mixture was refluxed for 1 hour
4. filtrationThe solution was filtered
5. additionwater (15 ml) was added
6. additionSolid NaOH was added until pH>>10
7. extractionthe solution was extracted with CH2Cl2 (3×20 ml)
8. dry with materialThe organic layers were dried over Na2SO4
9. customevaporated until dryness

ORD record

ord-cd8d159658c44b6aaaee908c220b336a

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06242409B1